SU1373319A3 - Способ получени сложных эфиров пиридинилоксифеноксипропановой кислоты - Google Patents
Способ получени сложных эфиров пиридинилоксифеноксипропановой кислоты Download PDFInfo
- Publication number
- SU1373319A3 SU1373319A3 SU843739180A SU3739180A SU1373319A3 SU 1373319 A3 SU1373319 A3 SU 1373319A3 SU 843739180 A SU843739180 A SU 843739180A SU 3739180 A SU3739180 A SU 3739180A SU 1373319 A3 SU1373319 A3 SU 1373319A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- temperature
- reaction mixture
- mol
- mixture
- trifluoromethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 7
- 150000002148 esters Chemical class 0.000 title description 3
- 239000002253 acid Substances 0.000 title description 2
- 239000011541 reaction mixture Substances 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- WYYFNMXLUUHRAU-UHFFFAOYSA-N 2-phenoxy-2-pyridin-2-yloxypropanoic acid Chemical class C=1C=CC=NC=1OC(C(O)=O)(C)OC1=CC=CC=C1 WYYFNMXLUUHRAU-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- XWBHCJMXMDVYLP-UHFFFAOYSA-N 2-pyridin-2-yloxyphenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=N1 XWBHCJMXMDVYLP-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 230000007423 decrease Effects 0.000 abstract description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 230000000269 nucleophilic effect Effects 0.000 abstract 1
- 150000003151 propanoic acid esters Chemical class 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- ABNQGNFVSFKJGI-UHFFFAOYSA-N 2,3-dichloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CN=C(Cl)C(Cl)=C1 ABNQGNFVSFKJGI-UHFFFAOYSA-N 0.000 description 7
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- JLEJCNOTNLZCHQ-UHFFFAOYSA-N methyl 2-chloropropanoate Chemical compound COC(=O)C(C)Cl JLEJCNOTNLZCHQ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- -1 trifluoromethyl (pyridinyl-2-hydroxy) phenol Chemical compound 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- AQIHDXGKQHFBNW-ZCFIWIBFSA-N (2r)-2-(4-hydroxyphenoxy)propanoic acid Chemical compound OC(=O)[C@@H](C)OC1=CC=C(O)C=C1 AQIHDXGKQHFBNW-ZCFIWIBFSA-N 0.000 description 1
- XIFCGIKPAAZFFS-UHFFFAOYSA-N 2,3-difluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC(C(F)(F)F)=CN=C1F XIFCGIKPAAZFFS-UHFFFAOYSA-N 0.000 description 1
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 1
- JFZJMSDDOOAOIV-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Cl)N=C1 JFZJMSDDOOAOIV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-L benzene-1,4-diolate Chemical compound [O-]C1=CC=C([O-])C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-L 0.000 description 1
- KATNUXHENWPMQJ-UHFFFAOYSA-N butyl 2-chloropropanoate Chemical compound CCCCOC(=O)C(C)Cl KATNUXHENWPMQJ-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49419683A | 1983-05-13 | 1983-05-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1373319A3 true SU1373319A3 (ru) | 1988-02-07 |
Family
ID=23963454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU843739180A SU1373319A3 (ru) | 1983-05-13 | 1984-05-11 | Способ получени сложных эфиров пиридинилоксифеноксипропановой кислоты |
Country Status (21)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2152931C2 (ru) * | 1995-06-06 | 2000-07-20 | Пфайзер Инк. | Способ получения производных 2-арилокси-4-хлорпиридина |
| RU2204552C2 (ru) * | 1998-03-24 | 2003-05-20 | Новартис Аг | Способ получения пропинилового эфира (r)(+)-2-[4-(5-хлор-3-фторпиридин-2-илокси)фенокси]пропионовой кислоты |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3678485D1 (de) * | 1985-04-01 | 1991-05-08 | Ciba Geigy Ag | 3-fluorpyridyl-2-oxy-phenoxy-derivate mit herbizider wirkung. |
| FR2598146B1 (fr) * | 1986-04-30 | 1989-01-20 | Rech Ind | Nouveau procede de preparation de fibrates. |
| GB8621689D0 (en) * | 1986-09-09 | 1986-10-15 | Ici Plc | Liquid crystal material |
| US6426429B1 (en) * | 2000-08-11 | 2002-07-30 | General Electric Company | Process for the preparation of hindered phosphites |
| CN116535351A (zh) * | 2023-05-04 | 2023-08-04 | 江苏瑞恒新材料科技有限公司 | 一种合成高效盖草能的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK154074C (da) * | 1974-10-17 | 1989-02-27 | Ishihara Sangyo Kaisha | Alfa-(4-(5 eller 3,5 substitueret pyridyl-2-oxy)-phenoxy)-alkan-carboxylsyrer eller derivater deraf til anvendelse som herbicider, herbicidt middel samt fremgangsmaader til bekaempelse af ukrudt |
| TR19824A (tr) * | 1977-07-21 | 1980-01-24 | Ishihara Sangyo Kaisha | Trilorometilpiridoksifenoksipropionik as tuerevleri ve bunlari ihtiva eden herbisidler |
| JPS5461182A (en) * | 1977-10-20 | 1979-05-17 | Ishihara Sangyo Kaisha Ltd | 2-phenoxy-5-trifluoromethylpyridine compounds |
| US4325729A (en) * | 1977-12-13 | 1982-04-20 | Ciba-Geigy Corporation | Herbicidal and plant growth regulating pyridyloxy-phenoxy-propionic acid derivatives |
| AU547854B2 (en) * | 1981-06-01 | 1985-11-07 | Dow Chemical Company, The | Preparation of pyridyloxyphenol compounds |
-
1984
- 1984-04-27 IL IL71668A patent/IL71668A/xx not_active IP Right Cessation
- 1984-04-30 NZ NZ208000A patent/NZ208000A/en unknown
- 1984-05-01 CA CA000453207A patent/CA1217192A/en not_active Expired
- 1984-05-04 AT AT84303020T patent/ATE27814T1/de not_active IP Right Cessation
- 1984-05-04 EP EP84303020A patent/EP0128658B1/en not_active Expired
- 1984-05-04 DE DE8484303020T patent/DE3464246D1/de not_active Expired
- 1984-05-08 AU AU27794/84A patent/AU561708B2/en not_active Ceased
- 1984-05-09 ZA ZA843493A patent/ZA843493B/xx unknown
- 1984-05-10 RO RO84114510A patent/RO89262A/ro unknown
- 1984-05-11 PL PL1984247642A patent/PL143532B1/pl unknown
- 1984-05-11 PT PT78576A patent/PT78576A/pt not_active IP Right Cessation
- 1984-05-11 YU YU00830/84A patent/YU83084A/xx unknown
- 1984-05-11 DK DK236684A patent/DK163503C/da not_active IP Right Cessation
- 1984-05-11 ES ES532444A patent/ES8606239A1/es not_active Expired
- 1984-05-11 SU SU843739180A patent/SU1373319A3/ru active
- 1984-05-11 HU HU841841A patent/HU189891B/hu not_active IP Right Cessation
- 1984-05-11 JP JP59094409A patent/JPS59212473A/ja active Granted
- 1984-05-11 DD DD84262952A patent/DD219477A5/de unknown
- 1984-05-12 KR KR1019840002562A patent/KR900006684B1/ko not_active Expired
- 1984-05-14 CS CS843566A patent/CS254974B2/cs unknown
- 1984-11-13 BR BR8402253A patent/BR8402253A/pt not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| Патент GB № 1599121, кл. С2С, 1981. Патент US 4046553, кл. С 07 D 213/30, 1977. * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2152931C2 (ru) * | 1995-06-06 | 2000-07-20 | Пфайзер Инк. | Способ получения производных 2-арилокси-4-хлорпиридина |
| RU2204552C2 (ru) * | 1998-03-24 | 2003-05-20 | Новартис Аг | Способ получения пропинилового эфира (r)(+)-2-[4-(5-хлор-3-фторпиридин-2-илокси)фенокси]пропионовой кислоты |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ208000A (en) | 1987-11-27 |
| ZA843493B (en) | 1985-12-24 |
| IL71668A (en) | 1988-07-31 |
| DE3464246D1 (en) | 1987-07-23 |
| HUT34429A (en) | 1985-03-28 |
| DK236684D0 (da) | 1984-05-11 |
| PT78576A (en) | 1984-06-01 |
| YU83084A (en) | 1986-10-31 |
| PL247642A1 (en) | 1985-03-26 |
| CA1217192A (en) | 1987-01-27 |
| KR840009297A (ko) | 1984-12-26 |
| KR900006684B1 (ko) | 1990-09-17 |
| AU561708B2 (en) | 1987-05-14 |
| EP0128658A1 (en) | 1984-12-19 |
| CS356684A2 (en) | 1987-07-16 |
| DK163503C (da) | 1992-07-27 |
| ES532444A0 (es) | 1985-11-01 |
| DD219477A5 (de) | 1985-03-06 |
| RO89262A (ro) | 1986-03-15 |
| ES8606239A1 (es) | 1985-11-01 |
| JPS59212473A (ja) | 1984-12-01 |
| AU2779484A (en) | 1984-11-15 |
| ATE27814T1 (de) | 1987-07-15 |
| IL71668A0 (en) | 1984-07-31 |
| JPH0475229B2 (enrdf_load_stackoverflow) | 1992-11-30 |
| DK163503B (da) | 1992-03-09 |
| EP0128658B1 (en) | 1987-06-16 |
| CS254974B2 (en) | 1988-02-15 |
| PL143532B1 (en) | 1988-02-29 |
| DK236684A (da) | 1984-11-14 |
| HU189891B (en) | 1986-08-28 |
| BR8402253A (pt) | 1984-12-18 |
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